CN100412120C - Thermoplastic composition containing polymeric anti-static salt, method of making, and use thereof - Google Patents
Thermoplastic composition containing polymeric anti-static salt, method of making, and use thereof Download PDFInfo
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- CN100412120C CN100412120C CNB2004800392093A CN200480039209A CN100412120C CN 100412120 C CN100412120 C CN 100412120C CN B2004800392093 A CNB2004800392093 A CN B2004800392093A CN 200480039209 A CN200480039209 A CN 200480039209A CN 100412120 C CN100412120 C CN 100412120C
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- China
- Prior art keywords
- poly
- salt
- alkyl
- acid
- static
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000003839 salts Chemical class 0.000 title claims abstract description 69
- 239000000203 mixture Substances 0.000 title claims abstract description 67
- 229920001169 thermoplastic Polymers 0.000 title claims abstract description 27
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000004416 thermosoftening plastic Substances 0.000 title description 10
- 239000004417 polycarbonate Substances 0.000 claims description 44
- 229920000515 polycarbonate Polymers 0.000 claims description 42
- 239000000178 monomer Substances 0.000 claims description 31
- 229920000642 polymer Polymers 0.000 claims description 28
- 125000000524 functional group Chemical group 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- 150000002500 ions Chemical class 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 18
- 238000006116 polymerization reaction Methods 0.000 claims description 18
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- 238000000465 moulding Methods 0.000 claims description 15
- 150000001450 anions Chemical class 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- 238000007334 copolymerization reaction Methods 0.000 claims description 8
- 229910052698 phosphorus Chemical group 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- 125000002091 cationic group Chemical group 0.000 claims description 7
- 239000011574 phosphorus Chemical group 0.000 claims description 7
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 229920002125 Sokalan® Polymers 0.000 claims description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 5
- 239000004584 polyacrylic acid Substances 0.000 claims description 5
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 229920006380 polyphenylene oxide Polymers 0.000 claims description 4
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 4
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 claims description 3
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 3
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 229920001470 polyketone Polymers 0.000 claims description 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 19
- 230000001747 exhibiting effect Effects 0.000 abstract description 2
- -1 perfluorinated alkyl sulphonate Chemical compound 0.000 description 52
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 23
- 230000003068 static effect Effects 0.000 description 21
- 239000000463 material Substances 0.000 description 19
- 239000002585 base Substances 0.000 description 16
- 239000000428 dust Substances 0.000 description 15
- 229910052760 oxygen Inorganic materials 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 14
- 239000003112 inhibitor Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 13
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
- 239000001301 oxygen Substances 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 238000005406 washing Methods 0.000 description 11
- 239000000654 additive Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 9
- 239000006096 absorbing agent Substances 0.000 description 9
- 230000000996 additive effect Effects 0.000 description 9
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 9
- 238000005516 engineering process Methods 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Natural products OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 229930185605 Bisphenol Natural products 0.000 description 6
- AJKQKRIUGVVATA-UHFFFAOYSA-N C1=CC=CC=C1.C(CCC)P Chemical compound C1=CC=CC=C1.C(CCC)P AJKQKRIUGVVATA-UHFFFAOYSA-N 0.000 description 6
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 6
- 239000012964 benzotriazole Substances 0.000 description 6
- 239000006085 branching agent Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 229960003742 phenol Drugs 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 5
- 238000001746 injection moulding Methods 0.000 description 5
- 125000005647 linker group Chemical group 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000002861 polymer material Substances 0.000 description 4
- 229960001755 resorcinol Drugs 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000009825 accumulation Methods 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 235000013844 butane Nutrition 0.000 description 3
- DLIJPAHLBJIQHE-UHFFFAOYSA-N butylphosphane Chemical compound CCCCP DLIJPAHLBJIQHE-UHFFFAOYSA-N 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 238000003760 magnetic stirring Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000006557 surface reaction Methods 0.000 description 3
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 3
- MPCADCULRRWDOX-UHFFFAOYSA-N 1,1'-biphenyl;phosphorous acid Chemical compound OP(O)O.C1=CC=CC=C1C1=CC=CC=C1 MPCADCULRRWDOX-UHFFFAOYSA-N 0.000 description 2
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 description 2
- SODQFLRLAOALCF-UHFFFAOYSA-N 1lambda3-bromacyclohexa-1,3,5-triene Chemical compound Br1=CC=CC=C1 SODQFLRLAOALCF-UHFFFAOYSA-N 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- HNURKXXMYARGAY-UHFFFAOYSA-N 2,6-Di-tert-butyl-4-hydroxymethylphenol Chemical compound CC(C)(C)C1=CC(CO)=CC(C(C)(C)C)=C1O HNURKXXMYARGAY-UHFFFAOYSA-N 0.000 description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- KLSLBUSXWBJMEC-UHFFFAOYSA-N 4-Propylphenol Chemical compound CCCC1=CC=C(O)C=C1 KLSLBUSXWBJMEC-UHFFFAOYSA-N 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 101150114104 CROT gene Proteins 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
- 206010013786 Dry skin Diseases 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- CUBCNYWQJHBXIY-UHFFFAOYSA-N benzoic acid;2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1O CUBCNYWQJHBXIY-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- TZSMWSKOPZEMAJ-UHFFFAOYSA-N bis[(2-methoxyphenyl)methyl] carbonate Chemical compound COC1=CC=CC=C1COC(=O)OCC1=CC=CC=C1OC TZSMWSKOPZEMAJ-UHFFFAOYSA-N 0.000 description 2
- 210000004271 bone marrow stromal cell Anatomy 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- QOQHDJZWGSAHFL-UHFFFAOYSA-N butylphosphanium;bromide Chemical compound [Br-].CCCC[PH3+] QOQHDJZWGSAHFL-UHFFFAOYSA-N 0.000 description 2
- 238000003490 calendering Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 238000000748 compression moulding Methods 0.000 description 2
- 238000002242 deionisation method Methods 0.000 description 2
- UZEFVQBWJSFOFE-UHFFFAOYSA-N dibutyl hydrogen phosphite Chemical compound CCCCOP(O)OCCCC UZEFVQBWJSFOFE-UHFFFAOYSA-N 0.000 description 2
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000005027 hydroxyaryl group Chemical group 0.000 description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 2
- 238000000520 microinjection Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 150000003902 salicylic acid esters Chemical class 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 125000005504 styryl group Chemical group 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 2
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- 238000005859 coupling reaction Methods 0.000 description 1
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical class C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 description 1
- ZYGPFXDREUDKDG-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound C1(CCCCC1)C#N.C1(CCCCC1)C#N ZYGPFXDREUDKDG-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- SRONXYPFSAKOGH-UHFFFAOYSA-N cyclopentadecane Chemical compound C1CCCCCCCCCCCCCC1 SRONXYPFSAKOGH-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 1
- FYIBPWZEZWVDQB-UHFFFAOYSA-N dicyclohexyl carbonate Chemical compound C1CCCCC1OC(=O)OC1CCCCC1 FYIBPWZEZWVDQB-UHFFFAOYSA-N 0.000 description 1
- ZQUZPFYNEARCQO-UHFFFAOYSA-N dinaphthalen-1-yl carbonate Chemical compound C1=CC=C2C(OC(OC=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 ZQUZPFYNEARCQO-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- RSNDQTNQQQNXRN-UHFFFAOYSA-N dodecyl dihydrogen phosphite Chemical compound CCCCCCCCCCCCOP(O)O RSNDQTNQQQNXRN-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000004049 embossing Methods 0.000 description 1
- 229920003247 engineering thermoplastic Polymers 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- RPHYLOMQFAGWCD-UHFFFAOYSA-N ethane;phenol Chemical compound CC.OC1=CC=CC=C1 RPHYLOMQFAGWCD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- HQIXACMMBRHSSY-UHFFFAOYSA-N fluorophosphonous acid Chemical compound OP(O)F HQIXACMMBRHSSY-UHFFFAOYSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005067 haloformyl group Chemical group 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
- MHERPFVRWOTBSF-UHFFFAOYSA-N methyl(phenyl)phosphane Chemical compound CPC1=CC=CC=C1 MHERPFVRWOTBSF-UHFFFAOYSA-N 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000009740 moulding (composite fabrication) Methods 0.000 description 1
- XBGNERSKEKDZDS-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]acridine-4-carboxamide Chemical compound C1=CC=C2N=C3C(C(=O)NCCN(C)C)=CC=CC3=CC2=C1 XBGNERSKEKDZDS-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000088 plastic resin Substances 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- SPVXKVOXSXTJOY-UHFFFAOYSA-O selenonium Chemical class [SeH3+] SPVXKVOXSXTJOY-UHFFFAOYSA-O 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 150000003384 small molecules Chemical group 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- BYMHXIQVEAYSJD-UHFFFAOYSA-M sodium;4-sulfophenolate Chemical compound [Na+].OC1=CC=C(S([O-])(=O)=O)C=C1 BYMHXIQVEAYSJD-UHFFFAOYSA-M 0.000 description 1
- MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- BXYHVFRRNNWPMB-UHFFFAOYSA-N tetramethylphosphanium Chemical compound C[P+](C)(C)C BXYHVFRRNNWPMB-UHFFFAOYSA-N 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000012745 toughening agent Substances 0.000 description 1
- BWPNIANVWARHPR-UHFFFAOYSA-N tridecyl dihydrogen phosphite Chemical compound CCCCCCCCCCCCCOP(O)O BWPNIANVWARHPR-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000007666 vacuum forming Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Abstract
Compositions exhibiting water resistant anti-static properties prepared from a thermoplastic polymer and a polymeric anti-static salt is disclosed.
Description
The cross reference of related application
The application requires U.S. provisional application No.60/533, the right of priority in 173 (December 30 2003 applying date).
Technical field
The present invention relates to contain the thermoplastic compounds of polymeric anti-static salt, particularly contain the transparent composition of polymeric anti-static salt.
Background technology
Most polymers or blend polymer are non-conductive.Thereby, when processing and use polymkeric substance, produce static charge accumulation.Charged polymer in-mold product can attract the small-particle dust, and therefore hinders smooth surface appearance.Be attracted to the minimizing that particle on the molded article surface also may cause the goods transparency.In addition, static charge may seriously be disturbed the production technique of this base polymer.
Static inhibitor is a small molecule material, and it can add in the polymkeric substance to reduce the tendency that their produce static charge, and maybe when having electric charge, these static inhibitor promote the dissipation of this type of electric charge.The normally hydrophilic in essence or ionic of static inhibitor.In the time of on being present in surface of polymer material, they promote transfer transport, and therefore eliminate the accumulation of static charge.Static inhibitor is used with two kinds of methods.A kind of method is used outside static inhibitor, by being sprayed in the surface or the impregnated polymer material is used.Second method is used inner static inhibitor, and it joins in the polymkeric substance in first being processed.The static inhibitor of using by this way must be heat-staple and work in-process can be moved to the surface.
Because there are many static inhibitor to have the main component of surfactant additive as them, suitable a kind of can according to circumstances therefrom the selection.Surfactivity can comprise in the moulding process migration of agents to product surface and eliminate ability at the static charge accumulation of product surface.Yet, when as inner-during the static inhibitor used, the anion surface activity additive is difficult to use because they consistency and uniformly dispersed aspect relatively poor and tend to decomposition or deterioration during when heating.Contain quaternary nitrogen (quarternary nitrogen) in the cation surface activating additive molecule, on the other hand, although the antistatic property of amophoteric surface active additive is good, however they only under limited situation, can use because their thermotolerance extreme differences.As for nonionic surface-active additives, they are more compatible with polymer materials, die down but on antistatic property, be inclined to, and their effect disappearances under normal temperature or high temperature in time.In addition, because the limited thermostability of these non-ionic surface active static inhibitor, the use of they and engineering thermoplastic resin such as aromatic polycarbonate also is restricted, because this resinoid is processed during this temperature.Therefore, this class surfactant additive influences the optical property of aromatic polycarbonate unfriendly.
Although metal organic sulfonate is reported, especially static inhibitor is used in the inside of using as the polycarbonate and the vibrin of molding under the high temperature, and not only the consistency with resin is not enough for they, and their thermotolerance is also not enough simultaneously.The negative consequence that consistency is not enough is, because this type of static inhibitor, the transparency characteristic of some polymer materials incurs loss.Salt (organic sulfonic acid De Phosphonium, ammonium salt) also is known, and particularly the An of perfluorinated alkyl sulphonate is with phosphonium salt.
Although present known static inhibitor can be buied, make thermoplastic compounds have the static inhibitor of good resistance antistatic property but still need further to improve to provide, this antistatic property still keeps good along with the prolongation of time and/or after being exposed to water.Preferably, provide this type of improvement and do not damage the optical property (comprising transparency) of thermoplastics.
Summary of the invention
In one embodiment, composition comprises thermoplastic polymer and polymeric anti-static salt.
In another embodiment, composition comprises aromatic thermoplastic polymer and polymeric anti-static salt.
In another embodiment, composition comprises polycarbonate, aromatic polycarbonate, (copolymerization) polyestercarbonate, aromatics (copolymerization) polyestercarbonate, its blend or comprises the combination of at least a above-mentioned polymkeric substance; Be the polymeric anti-static salt of about 0.1～about 10 weight % based on composition total weight, wherein polymeric anti-static salt comprises the polymer anion component with Phosphonium or ammonium cation component, and the polymer anion component derives from poly-(methyl) vinylformic acid, polyacrylic acid, poly-(ethyl) vinylformic acid, poly-(toxilic acid), poly-(vinyl sulfonic acid) or poly-(4-styrene sulfonic acid).
In another embodiment, a kind ofly make method transparent, antistatic article, comprise: blend thermoplastic polymer and polymeric anti-static salt are to form blend; With this blend of molding to form goods.
In another embodiment, a kind of preparation comprises the method for polymerization plasma polymer of monomers anti-static salt, wherein ion monomer comprises reactive functional groups and salt part, and wherein reactive functional groups is epoxy group(ing), vinyl, acrylate-based, (alkyl) acrylate-based, allyl group, styryl, acrylamido, (alkyl) acrylamido, crot(on)yl or the combination that comprises at least a above-mentioned group; Wherein salt partly is carboxylate salt or the sulfonate that comprises according to following Jie Gou De Phosphonium or ammonium cation component:
Wherein Q is nitrogen or phosphorus; R
1, R
2, R
3And R
4Be C independently of one another
1-C
20Alkyl, (C
6-C
12Aryl) C
1-C
10Alkyl, (C
1-C
10Alkyl) C
6-C
12Aryl or C
6-C
12Aryl.
In another embodiment, polymeric anti-static salt comprises the repeating unit according to following structure:
R wherein
5Be H or (C
1-C
6) alkyl; R
6Be H or (C
1-C
6) alkyl; R
7Be H or (C
1-C
6) alkyl; G
1Be O or S; G
2Be O, S or NR
8, R wherein
8Be H or (C
1-C
6) alkyl; L is one or more unit ethylene glycol, divalence (C
1-C
20) alkyl, divalence (C
6-C
12) aryl, divalence (C
1-C
20Alkoxyl group) C
1-C
20Alkyl, divalence (C
1-C
10Alkyl) C
6-C
12Aryl, divalence (C
6-C
12Aryl) C
1-C
10Alkyl, divalence (C
1-C
10Alkoxyl group) C
6-C
12Aryl or divalence (C
6-C
12Aryloxy) C
1-C
10Alkyl; J is carboxylate salt or sulfonate groups; With M be An Huo phosphonium cation component according to following structure:
Wherein Q is nitrogen or phosphorus; R
1, R
2, R
3And R
4Be C independently of one another
1-C
20Alkyl, (C
6-C
12Aryl) C
1-C
10Alkyl, (C
1-C
10Alkyl) C
6-C
12Aryl or C
6-C
12Aryl.
Embodiment
Transparent, water-fast antistatic composition here are provided, comprise thermoplastic polymer and polymeric anti-static salt.This type of composition exhibiting goes out permanent antistatic property, and this antistatic property still keeps after surface washing.Be not wishing to be bound by theory,, believe that it is water-fast,, also allow static resistance to keep even therefore after washing because polymeric anti-static salt is high-molecular weight.
Here also disclose a kind of method that gives the goods permanent antistatic performance, these goods are prepared by thermoplastic polymer, and this method comprises the polymeric anti-static salt that adds significant quantity in thermoplastic polymer.
In one embodiment, preparation comprises the method for polymerization plasma polymer of monomers anti-static salt, and wherein ion monomer comprises reactive functional groups and salt functional group.
In another embodiment, polymeric anti-static salt comprises the reaction product of ion monomer, and wherein ion monomer comprises reactive functional groups and salt functional group.
Disclosed hereinly comprise all scopes and (for example, scope " about at the most 25 weight % expect to be about 5 weight %～about 20 weight % " is all intermediate values etc. that comprise end points and scope " about 5 weight %～about 25 weight % ") capable of being combined.
Term " halo " or " halogen " are meant fluorine, chlorine, bromine and iodine.
Term " haloalkyl " is meant the alkyl that comprises one or more halogen atoms, and wherein halogen atom replaces available hydrogen atom and replaces until perhalogenation.
Here " (methyl) acrylate " of Shi Yonging is to comprise acrylate and methacrylate functional.
Here the term of Shi Yonging " monomer " is to comprise monomer and oligopolymer, except as otherwise noted.
Here the polymeric anti-static salt of Shi Yonging can be any suitable polymer salt, and when with the thermoplastic polymer blend, it provides the transparent material that shows antistatic property.Polymeric anti-static salt generally comprises polymer anion component and cationic components, and is preferably non--the polymer cation component.The limiting examples of the polymer anion component that is fit to comprises the polyacid (poly (acids)) with polymer backbone, and this polyacid comprises a plurality of acidic-groups that dangle that can form ionic linkage with cationic components.The acidic-group that is fit to comprises, for example, and carboxylic acid and sulfonic acid.The skeleton of polymer anion component can be the substituent carbon skeleton that contains except that acid group, for example comprises line style, branching or ring-type C
1-C
10Alkyl, C
6-C
12Aryl, (C
1-C
10Alkyl) C
6-C
12Aryl and/or (C
6-C
12Aryl) C
1-C
10Alkyl, wherein each alkyl or aryl can be not replace or replace with 1,2 or 3 substituting group, this substituting group is independently selected from hydroxyl, halogen, C
1-C
6Alkyl, C
1-C
6Haloalkyl, C
1-C
6Alkoxyl group etc.
The limiting examples of polymer anion component comprises those that derive from poly-(methyl) vinylformic acid, polyacrylic acid, poly-(ethyl) vinylformic acid, poly-(toxilic acid), poly-(vinyl sulfonic acid), poly-(4-styrene sulfonic acid) etc.
The number-average molecular weight of polymer anion component (Mn) can for about 500～about 20,000, preferred about 1000～about 10,000, more preferably from about 2000～about 8,000, and more preferably from about 4000～about 7000.
Polymeric anti-static salt further comprises cationic components.The cationic components Bao Kuo Phosphonium or the ammonium cation that are fit to.The preferred cation component is the basis compound of array structure down:
Wherein Q is nitrogen or phosphorus; R
1, R
2, R
3And R
4Be C independently of one another
1-C
20Alkyl, (C
6-C
12Aryl) C
1-C
10Alkyl, (C
1-C
10Alkyl) C
6-C
12Aryl or C
6-C
12Aryl.The C that is fit to
1-C
20Alkyl comprises, for example, and methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, the tertiary butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, lauryl, stearyl etc.The limiting examples of Phosphonium or ammonium cation comprises, tetramethyl phosphonium, Si Yi Ji Phosphonium, Si Bing Ji Phosphonium, 4-butyl-phosphonium, triethyl Jia Ji Phosphonium, tributyl Jia Ji Phosphonium, tributyl Yi Ji Phosphonium, San Xin base Jia Ji Phosphonium, trimethyl Ding Ji Phosphonium, trimethylammonium Xin Ji Phosphonium, trimethylammonium Yue Gui Ji Phosphonium, trimethylammonium Ying Zhi Ji Phosphonium, triethyl Xin Ji Phosphonium or their ammonium analogue (ammonium analogs) etc.; With fragrant family Phosphonium such as tetraphenylphosphoniphenolate, three phenyl methyl Phosphonium, triphenyl benzyl base Phosphonium, tributyl benzyl base Phosphonium or their ammonium analogue etc.
Polymeric anti-static salt can be according to several synthetic route preparations.For example, (such as poly-(methacrylic acid) sodium salt) can (I) De Phosphonium or ammonium salt (such as the 4-butyl-phosphonium bromide) combine, and use known technology to form required polymeric anti-static salt with structure for polyacid or its corresponding salt.Alternatively, ion monomer can polymerization form polymeric anti-static salt.
In one embodiment, polymeric anti-static salt can be prepared by the polymerization plasma monomer, and this ion monomer comprises reactive functional groups and can give the salt part of antistatic property.Prepare polymeric anti-static salt by ion monomer via the polymerization of reactive functional groups, it comprises based on the polymer backbone of reactive group and the salt part on this skeleton of dangling.The reactive functional groups that is fit to can comprise, for example epoxy group(ing); The olefinic unsaturated functional group is as vinyl, acrylate-based, (C
1-C
6Alkyl) acrylate-based, allyl group, styryl, acrylamido, (C
1-C
6Alkyl) acrylamido, crot(on)yl etc.; Combination with above-mentioned reactive functional groups.Preferred reactive functional groups comprises that (methyl) is acrylate-based.
The salt part of ion monomer can comprise that for example, sulfonate comprises ammonium sulfonate (ammoniumsulfonate salt), Phosphonium sulfonate etc.; Carboxylate salt comprises ammonium carboxylate salt (ammonium caroxylatesalt), Phosphonium carboxylate salt etc.; With imidazole salts etc.The An that is fit to He phosphonium cation comprise described herein those.
Linking group may reside in the ion monomer, connects salt and partly arrives reactive functional groups.Any suitable linking group can use, and comprises divalence, that replace or unsubstituted alkyl, aryl, alkaryl, aralkyl etc.; Comprise the ether of one or more ethylene glycol unit etc.; Ester; Ketone; Acid amides; Urea; Carbonic ether; Carbamate etc.For example, on phenyl ring, have the styrene monomer that sulfonate replaces and have the phenyl linking group that reactive functional groups (olefinic is unsaturated) is connected to salt.In another embodiment, 4-(6-methacryloxy hexyl) oxygen base benzene (oxy benzene) 4-butyl-phosphonium sulfonate (its synthetic will be described below) contains hexyloxy benzene (hexyloxybenzene) linking group.
In exemplary embodiment, ion monomer has following general formula: (RF-)
mL (X)
n, wherein RF is a reactive functional groups, and X is the salt part, and L is a linking group; M is 1,2 or 3 integer; With n be 1,2 or 3 integer.In one embodiment, m be 1 and n be 1.Preferred reactive functional groups (RF) comprises aforesaid reactive functional groups.Preferred salt part (X) comprise described herein those, comprise that wherein cationic moiety can be the carboxylate salt or the sulfonate of An Huo phosphonium cation.Preferred linking group (L) comprises one or more ethylene glycol unit, divalence (C
1-C
20) alkyl, divalence (C
6-C
12) aryl; Divalence (C
1-C
10Alkyl) C
6-C
12Aryl, wherein to moieties, X is connected to aryl moiety to RF by covalently bound; Divalence (C
6-C
12Aryl) C
1-C
10Alkyl; Divalence (C
1-C
10Alkoxyl group) C
6-C
12Aryl; Divalence (C
6-C
12Aryloxy) C
1-C
10Alkyl etc.
Anti-static salt as the homopolymer that is prepared by the single ionic monomer type is preferred.Here also can use ion monomer to react the multipolymer for preparing with one or more other different ions monomers and/or non-ionic monomer by one type.Here the non-ionic monomer of Shi Yonging is that shortage salt functional group has the monomer as at least a reactive functional groups described herein simultaneously.By regulating ion monomer, other ion monomer and/or the type and the amount of non-ionic monomer, the performance of the polymeric anti-static salt that can designing institute gets is to be used for special requirement.The exemplary performance that can regulate comprises hydrophobicity, wetting ability, molecular weight, thermostability, consistency, transparency etc.
Optional, polymerization starter can be used for preparing from ion monomer the polymerization process of polymeric anti-static salt.Those of ordinary skills can determine to use optimal polymerization starter based on the reactive functional groups of ion monomer.The cationic polymerization initiators that is suitable for the polymerization epoxy-functional comprises, for example, aromatics salt such as iodine, sulfonium (sulfonium), bromine or
(selenonium) salt etc. comprises the U.S. patent No.4 that is described in Smith, those salt initiators in 250,053.
Polymerization starter can comprise the radical initiator based on peroxide, and this type of radical initiator promotes polymerization under thermal activation.Useful peroxy initiator example comprises, for example, benzoyl peroxide, dicumyl peroxide, methylethyl ketone peroxide, lauryl peroxide, cyclohexanone peroxide, t-butyl hydroperoxide, t-butyl hydroperoxide benzene, cross sad tertiary butyl ester, 2,5-dimethylhexane-2, the 5-dihydro-peroxidase, 2,5-dimethyl-2,5-two (t-butylperoxy)-oneself-3-alkynes, di-t-butyl peroxide, the tert-butyl peroxide cumyl, α, α '-two (t-butylperoxy--sec.-propyl) benzene, 2,5-dimethyl-2,5-two (t-butylperoxy) hexane, dicumyl peroxide, two (t-butylperoxy isophthalic esters, tert butyl peroxy benzoate, 2, two (tert-butyl peroxide) butane of 2-, 2, two (tert-butyl peroxide) octanes of 2-, 2,5-dimethyl-2,5-two (benzoyl peroxide) hexane, two (trimethyl silyl) superoxide, trimethyl silyl phenyl triphenyl silyl superoxide etc., and the combination that comprises at least a above-mentioned polymerization starter.
Azo type free base initiator also is fit to, for example, 2,2 '-Diisopropyl azodicarboxylate (AIBN), 2,2 '-azo two (2,4 dimethylpentane nitrile), 2,2 '-azo two (2-methylbutane nitrile), 1,1 '-azo (cyclohexane nitrile (cyclohexane carbonitrile)), 4,4 '-two (4-cyano group penta (the cyanopentanoic)) acid of azo etc.
Other polymerization starter comprises can promote reactive functional groups polymeric light trigger when being exposed to actinic radiation.This photoinitiator comprises the phosphine oxide light trigger, based on the light trigger of ketone, as hydroxyl-and alkoxyalkyl phenyl ketone, alkylthio phenylmorpholine base alkyl ketone, benzoin ether light trigger etc., and the combination that comprises at least a above-mentioned polymerization starter.
The amount of operable polymerization starter is about 0.1～about 10 weight % based on initiator and ion monomer gross weight, preferred about 1～about 8 weight %, and 2～about 5 weight % more preferably from about.
In one embodiment, polymeric anti-static salt comprises the repeating unit according to following structure (II):
R wherein
5Be H or (C
1-C
6) alkyl; R
6Be H or (C
1-C
6) alkyl; R
7Be H or (C
1-C
6) alkyl; G
1Be O or S; G
2Be O, S or NR
8, R wherein
8Be H or (C
1-C
6) alkyl; L is one or more unit ethylene glycol, divalence (C
1-C
20) alkyl, divalence (C
6-C
12) aryl, divalence (C
1-C
20Alkoxyl group) C
1-C
20Alkyl, divalence (C
1-C
10Alkyl) C
6-C
12Aryl, divalence (C
6-C
12Aryl) C
1-C
10Alkyl, divalence (C
1-C
10Alkoxyl group) C
6-C
12Aryl or divalence (C
6-C
12Aryloxy) C
1-C
10Alkyl; J is carboxylate salt or sulfonate groups; With M be An Huo phosphonium cation component according to following structure (III):
Wherein Q is nitrogen or phosphorus; R
1, R
2, R
3And R
4Be C independently of one another
1-C
20Alkyl, (C
6-C
12Aryl) C
1-C
10Alkyl, (C
1-C
10Alkyl) C
6-C
12Aryl or C
6-C
12Aryl.
In another embodiment, polymeric anti-static salt comprises the repeating unit according to structure (II), wherein R
5Be H or methyl, R
6And R
7Be H, and G
1And G
2Be O.In another embodiment, polymeric anti-static salt comprises the repeating unit according to structure (II), wherein R
5Be H or methyl, R
6And R
7Be H, G
1And G
2Be O; L is divalence (C
1-C
10Alkoxyl group) C
6-C
12Aryl; J is a sulfonate groups; With M Shi phosphonium cation component.
The amount that is present in the polymeric anti-static salt in the composition is about 0.1～about 10 weight % based on composition total weight, preferred about 0.5～about 8 weight %, 1～about 5 weight % more preferably from about, and 2～about 3 weight % more preferably from about.
Can comprise with the thermoplastic polymer that is fit to of polymeric anti-static salt combination, for example, aromatic thermoplastic polymer, polycarbonate, polyester, polyphenylene oxide, polyphenylene oxide/styrene blend, polymeric amide, polyketone, acrylonitrile-butadiene-styrene copolymer, its blend or comprise the combination of at least a above-mentioned polymkeric substance.
The preferred thermoplastic polymkeric substance is a polycarbonate, comprises that the multipolymer of aromatic polycarbonate, polyester, (copolymerization) polyestercarbonate, aromatic polycarbonate or it comprise the blend with the blend of other thermoplastic polymer.
Polycarbonate comprises the composition of (IV) structural unit that has formula:
Wherein R ' group sum at least about 60% being the aromatics organic group, rest part is aliphatic series or alicyclic group.Preferably, R ' be the aromatics organic group and, more preferably, the group of formula V:
-A
1-Y
1-A
2- (V)
Each A wherein
1And A
2Be the monocycle divalent aryl, Y
1Be to have bridged group zero, one or two atom, it separates A
1And A
2In exemplary embodiment, with an atom separates A
1And A
2The illustrative example of the type free radical is-O-,-S-,-S (O)-,-S (O)
2-,-C (O)-, methylene radical, cyclohexyl-methylene radical, 2-[2,2,1]-the inferior heptyl of dicyclo, ethylidene, isopropylidene, new pentylidene, cyclohexylidene, inferior cyclopentadecane base, encircle inferior dodecyl, inferior adamantyl etc.Bridged group Y
1Can be alkyl or saturated hydrocarbyl, as methylene radical, inferior suberyl or isopropylidene.In another embodiment, zero atom separates A
1And A
2, replace covalent linkage to connect A
1To A
2
Polycarbonate in general, can comprise surface reaction and melt polymerization by known technology manufacturing.For example, polycarbonate can be produced by the dihydroxy compound surface reaction, wherein atom separates A only
1And A
2Here the term of Shi Yonging " dihydroxy compound " comprises, for example, has the bisphenol cpd of following general formula (VI):
R wherein
aAnd R
bRepresent hydrogen, halogen atom independently of one another, preferred bromine or univalence hydrocarbyl; P and q are 0～4 integer independently of one another; And X
aThe group of representing a formula (VII):
-O-，-S-，
R wherein
cAnd R
dRepresent hydrogen atom or unit price line style or cyclic hydrocarbon radical independently of one another, and R
eBe bivalent hydrocarbon radical, oxygen or sulphur.
Can comprise two (hydroxyaryl) alkane series by the example of the bisphenol cpd type of formula (VII) expression, for example 1, two (4-hydroxyphenyl) methane of 1-; 1, two (4-hydroxyphenyl) ethane, 2 of 1-, two (4-hydroxyphenyl) propane (or dihydroxyphenyl propane) of 2-; 2, two (3, the 5-two bromo-4-hydroxyphenyl) propane of 2-; 2, two (3, the 5-dimethyl-4-hydroxyphenyl) propane of 2-; 2, two (4-hydroxyphenyl) butane of 2-; 2, two (4-hydroxyphenyl) octanes of 2-; 1, two (4-hydroxyphenyl) propane of 1-; 1, two (4-hydroxyphenyl) normal butanes of 1-; Two (4-hydroxyphenyl) toluene (phenylmethane); 2, two (4-hydroxyl-1-aminomethyl phenyl) propane of 2-; 1, two (4-hydroxyl-tert-butyl-phenyl) propane of 1-; 2, two (4-hydroxyl-3-bromophenyl) propane of 2-; 1, two (4-hydroxyphenyl) decane of 1-; 4, the 4-dihydroxydiphenyl ether; 4,4-sulfo-biphenol; 4,4-dihydroxyl-3,3-dichloro diphenyl ether; 4,4-dihydroxyl-2,5-dihydroxydiphenyl ether etc.; Two (hydroxyaryl) naphthenic hydrocarbon series, for example 1, two (4-hydroxyphenyl) pentamethylene of 1-; 1, two (4-hydroxyphenyl) hexanaphthenes of 1-; 1, two (3, the 5-dimethyl-4-hydroxyphenyl) hexanaphthenes of 1-; 1, two (4-hydroxyphenyl) cyclododecanes of 1-; 1, two (3, the 5-dimethyl-4-hydroxyphenyl) cyclododecanes of 1-; 1,1-is two-(4-hydroxyphenyl)-3,3,5-trimethyl-cyclohexane etc., or comprise the combination of at least a above-mentioned bisphenol cpd.
Can comprise wherein X by other example of the bisphenol cpd of formula (VI) expression
aFor-O-,-S-,-S (O)-or-S (O)
2-those, as 4,4 '-dihydroxydiphenyl ether, 4,4 '-dihydroxyl-3,3 '-3,5-dimethylphenyl ether etc.; Two (hydroxyl diaryl) thioethers (sulfide), as 4,4 '-dihydroxyl diphenyl sulfide (diphenylsulfide), 4,4 '-dihydroxyl-3,3 '-the dimethyl diphenyl sulfide etc.; Two (hydroxyl diaryl) sulfoxide, as, 4,4 '-dihydroxyl thionyl benzene, 4,4 '-dihydroxyl-3,3 '-the dimethyl thionyl benzene etc.; Two (hydroxyl diaryl) sulfone, as 4,4 '-dihydroxy diphenylsulphone, 4,4 '-dihydroxyl-3,3 '-diphenylsulfone dimethyl etc.; Or comprise the combination of at least a above-mentioned bisphenol cpd.
Other dihydroxy compound that can be used for polycarbonate polycondensation is represented by formula (VIII):
Wherein, R
fBe halogen atom, have an alkyl that the hydrocarbyl group of 1～15 carbon atom or halogen replace; N is 0～4 value.Halogen is bromine preferably.When n is 2 at least, R
fCan be identical or different.Can be by the examples for compounds of formula (VIII) expression, resorcinol compound for Resorcinol, replacement, as oreinol diphenol, 5-ethyl resorcinol, 5-propyl group Resorcinol, 5-butyl Resorcinol, 5-tert-butyl resorcin, 5-phenyl Resorcinol, 5-cumyl Resorcinol, 2,4,5,6-tetrafluoro Resorcinol, 2,4,5,6-tetrabromo Resorcinol etc.; Catechol; Quinhydrones; The quinhydrones that replaces is as 2-toluhydroquinone, 2-ethyl quinhydrones, 2-propyl group quinhydrones, 2-butylhydroquinone, 2-tertiary butylated hydroquinone, 2-phenyl quinhydrones, 2-cumyl quinhydrones, 2,3,5,6-duroquinol, 2,3,5,6-tetra-tert quinhydrones, 2,3,5,6-tetrafluoro quinhydrones, 2,3,5,6-tetrabromo quinhydrones etc.; Or comprise the combination of at least a above-claimed cpd.
Bisphenol cpd, for example by 2,2,2 of following formula (IX) expression ', 2 '-tetrahydrochysene-3,3,3 ', 3 '-tetramethyl--1,1 '-spiral shell is two-[1H-indenes]-6,6 '-glycol also can be used as dihydroxy compound:
Typical carbonate precursor comprises carbonyl halides (carbonyl halide), for example carbonyl chloride (phosgene) and carbonyl bromide; Two haloformates, for example dihydric phenol (dihydric phenol) is as two haloformates of dihydroxyphenyl propane, quinhydrones etc. and two haloformates of glycol such as ethylene glycol and neopentyl glycol; And diaryl carbonate, as diphenyl carbonate, carbonic acid two (tolyl) ester and carbonic acid two (naphthyl) ester.The carbonate precursor that is preferred for surface reaction is a carbonyl chloride.
The blend of the polycarbonate of branching and linear polycarbonate and branching polycarbonate also can use.Branching polycarbonate can prepare by add branching agent in polymerization process.These branching agents can comprise the polyfunctional group organic compound that contains at least three functional groups, and functional group can be hydroxyl, carboxyl, carboxylic acid anhydride, halo formyl radical and the combination that comprises at least a above-mentioned branching agent.Specific examples comprises trimellitic acid, trimellitic acid 1,2-anhydride, trimellitic acid trichloride (trimellitic trichloride), three p-hydroxybenzene ethane, isatin-biphenol, trisphenol TC (1; 3; 5-three ((to hydroxyphenyl) sec.-propyl) benzene), trisphenol PA (4 (4 (1; two (to the hydroxyphenyl)-ethyls of 1-) α; α-Er Jiajibianji) phenol), 4-chloroformyl Tetra hydro Phthalic anhydride, trimesic acid, benzophenone tetracarboxylic acid etc., or comprise the combination of at least a above-mentioned branching agent.Based on the polycarbonate gross weight, branching agent adds with the content of about 0.05～about 2.0 weight % (wt%).The method that branching agent and being used to is made branching polycarbonate is described in U.S. patent Nos.3, in 635,895 and 4,001,184.
All types of polycarbonate terminal groups all can be used for polycarbonate compositions.The example of some common polycarbonate terminal groups is phenol (phenol), to cumyl phenol (PCP) and tert.-butyl phenol.
In one embodiment, polycarbonate can be by the melt polycondensation reaction production between dihydroxy compound and the carbonic diester.The example that can be used for producing the carbonic diester of polycarbonate is diphenyl carbonate, carbonic acid two (2, the 4-dichlorophenyl) ester, carbonic acid two (2,4, the 6-trichlorophenyl) tolyl ester, carbonic acid dinaphthyl ester, diphenyl carbonate, diethyl carbonate, methylcarbonate, dibutyl carbonate, carbonic acid dicyclohexyl ester, two (guaiacyl) esters of carbonic acid (two cresotinic acid acid esters of carbonic acid between ester, two (2-cyano-phenyl) esters of carbonic acid, two (ortho-nitrophenyl base) esters of carbonic acid, carbonic acid ditolyl ester, carbonic acid, or comprise the combination of at least a above-mentioned carbonic diester BMSC) etc..Preferred carbonic diester is diphenyl carbonate and BMSC.
(copolymerization) polyestercarbonate also is fit to, have another name called (copolymerization) polyester-polycarbonate or polyestercarbonate, that is, also contain repetition or reappear the unitary resin of carboxylicesters (carboxylate) except that reproduction polycarbonate (polycarbonate) chain unit of formula (X), its Chinese style (X) is:
Wherein D is the divalent group that is applied to the dihydroxy compound of polyreaction, and dihydroxy compound as previously mentioned; Repeat or reproduction carboxylic ester units, for example formula (XI):
Wherein D as defined above, T is phenylene of aromatic group such as phenylene, naphthylidene, biphenylene, replacement etc.; Divalence aliphatics-aromatic hydrocarbon radical is as alkaryl or alkylaryl group; Or two or more are by the aromatic group that this type of aromatics key connects, and this is that prior art is known.
Copolyesters-polycarbonate resin is also by interfacial polymerization technology preparation, be well known by persons skilled in the art (referring to, for example, U.S. patent Nos.3,169,121 and 4,487,896).
The example of dicarboxylic acid comprises m-phthalic acid, terephthalic acid and has the α of 6～18 carbon atoms, ω aliphatic diacid.Preferably (copolymerization) polyestercarbonate is m-phthalic acid, terephthalic acid and the Resorcinol that has or do not have BPA.In general, any dicarboxylic acid that is used to prepare linear polyesters can be used for the preparation of polyestercarbonate resin.Generally, operable dicarboxylic acid comprises aliphatic dicarboxylic acid, aromatic dicarboxylic acid and aliphatics aromatic dicarboxylic acid.These acid are known and are disclosed in, for example, and in the U.S. patent 3,169,121.Can use the mixture of dicarboxylic acid.Be m-phthalic acid, terephthalic acid and their mixture preferably as aromatic dicarboxylic acid.Useful especially bifunctional carboxylic acid comprises the mixture of m-phthalic acid and terephthalic acid, and wherein the weight ratio of terephthalic acid and m-phthalic acid is about 10: 1～about 0.2: 9.8.
Utilize dicarboxylic acid itself with it, can, use this sour reactive derivatives sometimes even preferably.These reactive derivatives are acyl halide for example.Preferred acyl halide is acyl group dichloro (acid dichloride) and acyl group dibromo (acid dibromide).Therefore, for example replace the use of m-phthalic acid, terephthalic acid or their mixture, can use isophthaloyl dichloro, terephthaloyl dichloro and their mixture.
The blend of PC and other compatible polymer also can be used for this composition.Examples of such polymers comprises polybutylene terephthalate and styrene-butadiene rubber(SBR), as ABS or MBS rubber.The ratio of other compatible polymer and PC can be up to 50: 50, or bigger.
Thermoplastic compounds also can comprise various optional components, comprises UV absorption agent, Phosphorus stablizer, for example oxidation retarder, Hinered phenols oxidation retarder, epoxies stablizer and sulphur class stablizer etc.
Any uv-absorbing agent that is generally used for resin combination can be used as above-mentioned uv-absorbing agent.For example, can use benzotriazole category uv-absorbing agent, benzophenone uv-absorbing agent or salicylate class uv-absorbing agent etc.The example of benzotriazole category uv-absorbing agent comprise 2-(2 '-hydroxyl-5 '-aminomethyl phenyl) benzotriazole, 2-(2 '-hydroxyl-5 '-tert-butyl-phenyl) benzotriazole, 2-(2 '-hydroxyl-5 '-uncle's octyl phenyl) benzotriazole, 2-(2 '-hydroxyl-3 ', 5 '-two-tert-butyl-phenyl) benzotriazole, 2-(2 '-hydroxyl-3 ', 5 '-the diamyl butyl phenyl) benzotriazole, 2-(2 '-hydroxyl-3 '-dodecyl-5 '-aminomethyl phenyl) benzotriazole, 2-(2 '-hydroxyl-3 ', 5 '-dicumylphenyl) benzotriazole and 2,2 '-[4-(1 for methylene-bis, 1,3, the 3-tetramethyl butyl)-6-(2H-benzotriazole-2-yl) phenol] etc.For example, the benzotriazole category uv-absorbing agent is sold as UV5411 by American Cyanamid Co..In addition, the benzophenone uv-absorbing agent is sold as UV531 by American Cyanamid Co..The example of salicylate class uv-absorbing agent comprise salol, Whitfield's ointment to tert-butyl-phenyl ester and Whitfield's ointment to octyl phenyl ester etc.
The example of Phosphorus stablizer comprises triphenyl phosphite, phosphorous acid phenylbenzene nonyl ester, tricresyl phosphite (2, the 4-di-tert-butyl-phenyl) ester, Wytox 312, phosphorous acid phenylbenzene isooctyl acrylate, phosphorous acid 2,2 '-methylene-bis (4, the 6-di-tert-butyl-phenyl) octyl group ester, phosphorous acid phenylbenzene isodecyl ester, phosphorous acid phenylbenzene list (tridecyl) ester, fluoro phosphorous acid 2,2 '-ethylenebis (4, the 6-DI-tert-butylphenol compounds) ester, diisodecyl phenyl phosphite, phosphorous acid phenyl two (tridecyl) ester, tricresyl phosphite (2-ethylhexyl) ester, tricresyl phosphite (isodecyl) ester, tricresyl phosphite (tridecyl) ester, phosphorous acid dibutyl hydrogen ester (dibutylhydrogenphosphite), trithio tricresyl phosphite Lauryl Ester, four (2, the 4-di-tert-butyl-phenyl) 4,4 '-the biphenylene diphosphites, 4,4 '-isopropylidene biphenol alkyl (C
12-C
15) phosphorous acid ester, 4,4 '-two (3-methyl-6-tert butyl phenyl) the double tridecyl phosphorous acid esters of butylidene, two (2, the 4-di-tert-butyl-phenyl) pentaerythritol diphosphites, two (2,6-di-t-butyl-4-aminomethyl phenyl) pentaerythritol diphosphites, two (nonyl phenyl) pentaerythritol diphosphites, distearyl-pentaerythritol diphosphites, phenyl-dihydroxyphenyl propane pentaerythritol diphosphites, tetraphenyl dipropylidene diol diphosphites, 1,1,3-three (2-methyl-4-two-three decyls phosphorous acid ester-5-tert-butyl-phenyl) butane and 3,4,5,6-dibenzo-1,2-oxaphosphan-2-oxide compound etc.The commerical prod that can buy comprises Adekastab PEP-36, PEP-24, PEP-4C and PEP-8 (whole trade marks, make by Asahi Denka Kogyo K.K.), Irgafos 168 (trade marks, make by CibaSpecialty Chemicals.), Sandostab P-EPQ (trade mark, make by Clariant), ChelexL (trade mark, make by Sakai Kagaku Kogyo K.K.), 3P2S (trade mark, make by Ihara ChemicalKogyo K.K.), Mark 329K and Mark P (two trade marks, make by Asahi Denka Kogyo K.K.) and Weston 618 (trade mark is made by Sanko Kagaku K.K.).
The example of Hinered phenols oxidation retarder comprise Octadecane base-3-(3 ', 5 '-di-t-butyl 4-hydroxyphenyl) propionic ester, 2,6-di-t-butyl 4-hydroxymethyl phenol, 2,2 '-methylene-bis (4-methyl-6-tert butyl phenol) and tetramethylolmethane-four [3-(3,5-di-t-butyl 4-hydroxyphenyl) propionic ester etc.
The example of epoxies stablizer comprises epoxidised soya-bean oil, epoxidised Toenol 1140, phenyl glycidyl ether, glycidyl allyl ether and 3,4-epoxy group(ing) cyclohexyl methyl-3 ', 4 '-the epoxy-cyclohexane carboxylicesters etc.
Other additive commonly used can amount as required join in all resin combinations when mixed with resin or molding, and this additive does not have any deleterious effect on physicals.For example, can add tinting material (pigment or dyestuff), toughener (glass fibre, carbon fiber etc.), filler (carbon black, silica, titanium oxide etc.), heat-resistant agents, oxidation retarder, weather resisting agent, lubricant, releasing agent, softening agent, fire retardant and flow enhancing agent etc.In addition, can add dyestuff, so that revise the yellow on blue direction (bluedirection).
As for this method for compositions of preparation, can use the routine techniques of utilization standard equipment without any particular restriction ground, for example optional melting mixing of using a small amount of solvent.The component of composition can any order be mixed.The example of the device that is fit to is forcing machine, Banbury mixer, roller (roller) and the kneader etc. of intermittence or operate continuously.
Composition can use common thermoplastic process to change goods into, and this technology is the extruding of film and sheet material, injection moulding, gas aided injection mould, extrusion molding, compression molding and blowing for example.The expressing technique of film and sheet material can comprise and be not limited to fusion casting (melt casting), blown film is extruded and roll (calendaring).Coextrusion and laminating technology can be used to form composite multilayer membrane or sheet material.The single or multiple lift coating can further be applied to the single or multiple lift substrate to give additional properties, as anti-zoned property, ultraviolet resistance, aesthetic effect etc.Coating can be used by standard application techniques, for example roll extrusion, spraying, dipping, brushing or flow coat.Film of the present invention and sheet material can prepare by being casted into to remove to desolvate subsequently on substrate, band or the roller at the solution of the composition in the solvent that is fit to or suspension alternatively.
Alignment films can be by near blown film extrude or stretch casting or use conventional stretching technique calendered film to prepare heat-drawn wire.For example, radial extension is put instrument (stretching pantograph) and can be applied to multiaxis and stretch simultaneously; X-y direction stretching pantograph can be used for simultaneously or stretches at plane x-y direction of principal axis continuously.Equipment with continuous uniaxial extension part can also be used to obtain single shaft and biaxial stretching, as the machine that is used for carrying out tensile differential speed roll parts on machine direction and is used for the tenter machine parts of cross directional stretch is housed.
Composition can change multi-layer sheet into, this sheet material comprises having first side and second lateral first sheet material, with have first side and second lateral second sheet material, wherein first sheet material comprises thermoplastic polymer, and wherein first side arrangement of first sheet material on first side of a plurality of floors (rib); Wherein second sheet material comprises thermoplastic polymer, and wherein first side arrangement of second sheet material is on second side of a plurality of floors, and wherein first side of a plurality of floors is relative with second side of a plurality of floors.
Aforesaid film and sheet material can further be processed by thermoplasticity, form moulded products via moulding and molding process, and these operations are including, but not limited to thermoforming, vacuum forming, pressure forming, injection moulding and compression molding.Multilayer formed article also can be by technology as described below, and the injection heat plastic resin is on single or multiple lift film or sheet material substrate and form:
1. provide to have on the surface and choose any one kind of them or the single or multiple lift thermoplastic substrate of multiple color, for example use silk screen printing or dye transfer.
2. make substrate meet mold configuration,, and make this substrate and mould fit, this mould have surface with substrate 3D shape coupling for example by with the substrate moulding be trimmed to 3D shape.
3. inject the die cavity of thermoplastic resin to the substrate back, with the permanent bonded three-dimensional objects of (i) production integral type (one-piece) or (ii) from printed substrates transfer graphic or aesthetic effect (aesthetic effect) to the resin that injects, and remove this printed substrates, thereby give moulding resin with aesthetic effect.
Those skilled in the art also are appreciated that, common curing and surface modification technology can further be applied in the said products to change apparent and to give goods other function, and these technologies are including, but not limited to heat setting type, veining (texturing), embossing, corona treatment, flame treating, Cement Composite Treated by Plasma and vacuum moulding machine.
Therefore, another embodiment relates to goods, sheet material and the film by above preparation of compositions.Thermoplastic compounds is preferably used and is comprised, for example, and single or multiple lift sheet material or film product, household supplies, automobile application, eyeglass application, automotive lighting etc.
The composition that comprises thermoplastic polymer and polymeric anti-static salt also is provided here, and wherein the goods that prepared by said composition demonstrate the anti-fogging characteristic except that antistatic property.Do not wish bound by theory, but believe that the existence in the polymer anti static agent of product surface can reduce the surface tension of the water that may exist.Surface tension fully reduces, to stop the formation of water droplet.Do not form moisture film, and prevention forms mist on product surface.
The patent of all enumerating, patent application and other reference, its full content is hereby incorporated by.The present invention further describes with following non-restrictive example.
Embodiment
The preparation of poly-(methacrylic acid) tetrabutyl phosphonium salt (TBP-5) of polymeric anti-static salt:
(the 30 weight % aqueous solution, from Aldrich, Mn=6 500g/mol) is diluted by adding 50ml water poly-(methacrylic acid) sodium salt of 50 milliliters (ml) amount.In this solution, add gradually and be dissolved in the gram of 47.1 in 250ml water 4-butyl-phosphonium bromide, stirring simultaneously.Mixture stirs several minutes to react.At this moment, poly-(methacrylic acid) tetrabutyl phosphonium salt (TBP-5) formation that has structure (XII).TBP-5 300ml chloroform extraction, and in separating funnel, wash three times with 250ml water.Chloroform layer separates with water layer, and chloroform is removed (T by rotary evaporation
Beginning=40 ℃, T
Finish=90 ℃, P
Beginning=475 millibars, P
Knot Bundle=100 millibars) up to the TBP-5 drying.Product in vacuum drying oven (T=50 ℃) at least 12 hours with complete drying.
The preparation of TBP-5 and polycarbonate Alloys:
Several compositions that contain TBP-5 and polycarbonate prepare according to table 1.Blend is by preparing polymer salt and polycarbonate 175 (can derive from GE Plastics) compounding at 260 ℃.Polycarbonate stablizer Irgafos 168 (from Ciba Specialty Chemicals) (0.036 weight %) and Irganox 1076 (from Ciba Specialty Chemicals) (0.02 weight %) join in each prescription.Embodiment 4 further contains 4-butyl-phosphonium arylsulphonate EPA-202 (can derive from Takemoto Oil and Fat Co., Ltd.).
The plaque of each prescription (plaques) is 260 ℃ of injection speed injection mouldings with 15 and 35 seconds.The plaque that is used for electrostatic attenuation (static decay) and dust test (dust test) wraps in aluminium foil to protect the surface.
The electrostatic attenuation elimination half life values uses Honestometer type S5109 (Shishido Electrostatic Ltd.) to measure on the dull and stereotyped injected sample of 70 * 60 * 2.55 millimeters (mm).Charging potential is-10 kilovolts (kV).Result electrostatic attenuation elimination half life values (t
1/2, unit is second) and expression, the i.e. time of the electric-charge-dissipating of Huo Deing (dissipate) half.When measuring molding after the sample electrostatic attenuation time of (as-molded), plaque is with mobile deionization (DI) water washing, every 15 seconds, allowed under 23 ℃ and 50% relative humidity drying one day.The electrostatic attenuation time of washing back sample measures as mentioned above.
The dust test: the standard moisture eliminator wherein passes through 25% ammonia solution (NH as particle collector (dust chamber)
3Water) and the smog of 37% hydrogenchloride (HCl) combine and generate NH
4The artificial dust of Cl.Sample inserted particle collector one hour, carried out visual evaluation then.Sample is divided into ten ranks to estimate, and the dust of high level attracts to be labeled as 1 (difference), and the identified as samples that does not have dust to attract is designated as 10 (well).The cohesion (condense) on plaque amount of dust and the figure of accumulative dust all are contents of classification institute foundation.
The antidusting performance of table 1.TBP-5 and PC175 blend
aThe rank of dust test from 10 (whole plaque is all had fabulous antidusting performance) to 1 (poor)
bSome zone does not have dust
The presentation of results of table 1, TBP-5 join the antistatic and antidusting performance of having improved in the polycarbonate through the blend of washing.Though for the data presentation of the 0.6 weight %TBP-5 (embodiment 2 and 3) through washing, have dust to attract on some zones of molding plaque, have zone with no gray surface.Yet the concentration that increases TBP-5 all has fabulous dust experimental performance when causing whole molding plaque surface no matter to be molding or through the washing sample during to 2 weight % (embodiment 5).The dust experimental performance (embodiment 4) of sample when the adding of non--polymeric anti-static salt EPA-202 improves molding, but the properties of sample after the washing is better unlike the blend (not having EPA-202) of the TBP-5 with equivalent.This presentation of results, EPA-202 can not provide the maintenance of antistatic property after washing, this performance is provided by polymeric anti-static salt.
These blends are except that excellent in water resistance, antidusting performance, and optical property also is good, as shown in table 2.The yellowness index (YI) of the sample of 3.2 mm thick among the embodiment 1-5 obtains according to ASTMD1925.Light transmissive percentage ratio of composition (%) and haze value obtain according to ASTM D1003.
The optical property of table 2.TBP-5 and PC175 blend (3.2mm)
Show that slight YI increases although contain the blend of TBP-5, transmission % keeps high value.Find unexpectedly, the polymer anti static agent is joined the light transmission performance that will provide excellent in the transparent material and good haze results, excellent, permanent antistatic property are provided simultaneously.
Contain the preparation of poly-(methyl) acrylate (PMA-TBPS) of the 4-butyl-phosphonium sulfonate groups that dangles:
Synthesizing of 4-(6-hydroxyl hexyl) oxygen base benzene 4-butyl-phosphonium sulfonate:
In three mouthfuls of round-bottomed flasks that magnetic stirring bar and reflux exchanger are housed, add 4-hydroxy benzenesulfonic acid sodium salt (30.0 grams (g), 0.13mol), potassium hydroxide (9.0g, 0.16mol) and distilled water (60 milliliters (ml)).Under the room temperature, (23.16g 0.13mol) dropwise adds in this reaction mixture will to be dissolved in the 1-bromine hexanol of ethanol (50ml).Reaction mixture refluxed 24 hours is cooled to room temperature then.Sedimentary product is filtered, and wash to remove excessive 1-bromine hexanol with chloroform.Product under 70 ℃ of vacuum dry 12 hours obtains 4-(6-hydroxyl hexyl) the oxygen base benzene sulfonic acid sodium salt (92% productive rate) of 38.06g.
Exsiccant salt (21.0g) is dissolved in the deionized water (200ml), and (+H is Tulsion) to obtain 4-(6-hydroxyl hexyl) oxygen base Phenylsulfonic acid by ion exchange column.The aqueous solution of 4-(6-hydroxyl hexyl) oxygen base Phenylsulfonic acid reaches pH 7 with 4-butyl-phosphonium oxyhydroxide (TBPH) neutralization.The aqueous solution that produces chloroform extraction (3 * 100ml); (combined) organic layer of this combination washes with water, separates, and dry on anhydrous sodium sulphate.Filter organic solution, solvent is removed on rotatory evaporator, obtains colourless heavy-gravity 4-(6-hydroxyl hexyl) oxygen base benzene 4-butyl-phosphonium sulfonate.Product under 60 ℃ of vacuum dry 12 hours; Productive rate is 35g (94%).
Synthesizing of 4-(6-methacryloxy hexyl) oxygen base benzene 4-butyl-phosphonium sulfonate:
In three mouthfuls of round-bottomed flasks of the 250ml that magnetic stirring bar, nitrogen ingress pipe and dropping funnel are housed, add 4-(6-hydroxyl hexyl) oxygen base benzene 4-butyl-phosphonium sulfonate (20.0g, 0.038mol), dried chloroform (50ml), triethylamine (5.82g, 0.058mol) and catalytic amount 2,6-di-t-butyl-p-cresol.With salt ice reaction mixture is cooled to 5 ℃, and (5.51g added dropwise 0.058mol) with the methacrylic chloride in the dried chloroform (50ml) in the clock time at 30 minutes.Reaction mixture allows that reaching room temperature also further stirred 24 hours.Excessive methacrylic chloride and solvent are under reduced pressure removed, and obtain residue.Residue is with ethyl acetate (100ml) extraction, with the sodium bicarbonate aqueous solution (100ml) of ethyl acetate solution and 5% stirring 2 hours.The separating ethyl acetate layer, (2 * 50ml), drying on sodium sulfate is filtered with distilled water wash, solvent is removed on rotatory evaporator, obtains thickness oily (oily) product (75% productive rate) of 4-(6-methacryloxy hexyl) the oxygen base benzene 4-butyl-phosphonium sulfonate of 18g.
Poly-(methyl) acrylate (PMA-TBPS) synthetic that contains the 4-butyl-phosphonium sulfonate groups that dangles:
In three mouthfuls of round-bottomed flasks of the 250ml that magnetic stirring bar and nitrogen ingress pipe are housed, add 4-(6-methacryloxy hexyl) oxygen base benzene 4-butyl-phosphonium sulfonate (22.0g, 0.037mol), do 1,4-diox (90ml) and benzoyl peroxide (1.1g, 5 weight %).Reaction mixture was 90 ℃ of heating 24 hours.Solvent is under reduced pressure removed, and the thickness product that obtains is dissolved in the acetone (50ml), and precipitates in toluene (500ml).Toluene is by decant (decant), and the polymkeric substance of acquisition is 60 ℃ of dryings 24 hours under reduced pressure, obtains to contain poly-(methyl) acrylate of the 4-butyl-phosphonium sulfonate groups that dangles.
The preparation of PMA-TBPS and polycarbonate Alloys:
The antistatic property that contains poly-(methyl) acrylate of the 4-butyl-phosphonium sulfonate groups that dangles passes through itself and polycarbonate (PC145 derives from GE Plastics) are estimated with blend under the load that is 2 and 5 weight % based on polycarbonate and poly-(methyl) acrylate total amount.Blend comprises following additive: Tinuvin 234 (0.27 weight %), Irgaphos 168 (0.16 weight %), Irganox 1076 (0.04 weight %) and is used for the pentaerythritol tetrastearate (PETS of embodiment 6-7; 0.3 weight %).Mixed polycarbonate, salt and additive are about 1 minute in mixing and grinding machine (mixer-grinder).Recombined sample before the preparation sample in baking oven 80 ℃ of dryings at least 12 hours.The compounding then of the material of drying, and in twin screw little be mixed machine and micro-injection mould machine (micro-injection molder) (DACA Instruments) according to following condition injection moulding: the machine barrel zone temperature of being mixed is 280-285 ℃, screw speed is 100rpm, plasticizing chamber (transfer pot) temperature is that 275-280 ℃ and die temperature are 90 ℃.The injection moulding sample that produces has the size of 50mm * 35mm * 2mm.
On sample, measure the electrostatic attenuation elimination half life values of the blend of TBP-5 and polycarbonate according to above method.The result of electrostatic attenuation test and the visual inspection presentation of results of transparency are in table 3.
The antistatic property of poly-(methyl) acrylate of the 4-butyl-phosphonium sulfonate groups that table 3. containing in polycarbonate dangles
aDo not contain PETS
bWashing is after 60 seconds under flowing water
cWashing is after 10 seconds under flowing water
The result illustrates that in table 3 poly-(methyl) acrylate that will contain the 4-butyl-phosphonium sulfonate groups that dangles joins in the polycarbonate, obtains excellent antistatic property and keeps, even be exposed to after the flowing water.
When the present invention describes according to preferred embodiment, it will be appreciated by those skilled in the art that and to make various variations in the case without departing from the scope of the present invention and can be equal to replacement its key element.In addition, under the situation that does not deviate from essential scope of the present invention, can make many variations to adapt to special situation or material according to instruction of the present invention.Therefore, this means that the present invention is not limited to realizing the disclosed specific embodiments of best mode of the present invention's expection, the present invention will comprise that all belong to the embodiment of claim scope.
Claims (9)
1. composition comprises:
Thermoplastic polymer; With
Polymeric anti-static salt, wherein this polymeric anti-static salt comprises polymer anion component and cationic components, and this polymer anion component derives from polyacrylic acid, poly-(alkyl) vinylformic acid, poly-(toxilic acid), poly-(vinyl sulfonic acid), polyacrylic ester or poly-(alkyl) acrylate.
2. according to the composition of claim 1, wherein this thermoplastic polymer is polycarbonate, polyester, polyphenylene oxide, polyphenylene oxide/styrene blend, polymeric amide, polyketone, acrylonitrile-butadiene-styrene copolymer, its blend or the combination that comprises at least a above-mentioned polymkeric substance.
3. according to the composition of claim 1, wherein this polyacrylic ester or poly-(alkyl) acrylate comprise carboxylate radical or sulfonate group.
4. according to the composition of claim 1, wherein this polymeric anti-static salt is the reaction product of ion monomer and polymerization starter, and wherein this ion monomer comprises reactive functional groups and salt part.
5. according to the composition of claim 1, wherein this polymeric anti-static salt Bao Han Phosphonium or ammonium cation component.
6. according to the composition of claim 5, Phosphonium or ammonium cation component comprise the basis compound of array structure down in it:
Wherein Q is nitrogen or phosphorus; R
1, R
2, R
3And R
4Be C independently of one another
1-C
20Alkyl, (C
6-C
12Aryl) C
1-C
10Alkyl, (C
1-C
10Alkyl) C
6-C
12Aryl or C
6-C
12Aryl.
7. composition comprises:
Polycarbonate, aromatic polycarbonate, (copolymerization) polyestercarbonate, aromatics (copolymerization) polyestercarbonate, its blend or comprise the combination of at least a above-mentioned polymkeric substance; With
Based on the said composition gross weight is the polymeric anti-static salt of 0.1～10 weight %,
Wherein this polymeric anti-static salt comprises the polymer anion component with Phosphonium or ammonium cation component, and this polymer anion component derives from poly-(methyl) vinylformic acid, polyacrylic acid, poly-(ethyl) vinylformic acid, poly-(toxilic acid), poly-(vinyl sulfonic acid), comprise poly-(methyl) acrylate of sulfonic acid group or comprise the polyacrylic ester of sulfonic acid group; Perhaps wherein this polymeric anti-static salt is the reaction product of ion monomer, and wherein ion monomer comprises reactive functional groups and salt part.
8. goods by the preparation of compositions of claim 1.
9. the method for transparent, the antistatic article of a manufacturing comprises:
Blend thermoplastic polymer and polymeric anti-static salt are to form blend; With
This blend of molding is to form goods, wherein this polymeric anti-static salt comprises polymer anion component and cationic components, and this polymer anion component derives from polyacrylic acid, poly-(alkyl) vinylformic acid, poly-(toxilic acid), poly-(vinyl sulfonic acid), polyacrylic ester or poly-(alkyl) acrylate.
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| US53317303P | 2003-12-30 | 2003-12-30 | |
| US60/533,173 | 2003-12-30 | ||
| US10/815,257 | 2004-03-31 |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4450249A (en) * | 1979-08-01 | 1984-05-22 | Bayer Aktiengesellschaft | Internal antistatic agents for polycarbonates and for polycarbonate films |
| US5187214A (en) * | 1988-11-08 | 1993-02-16 | Ppg Industries, Inc. | Quaternary ammonium antistatic polymer compositions |
| EP0897950A2 (en) * | 1997-07-23 | 1999-02-24 | General Electric Company | Anti-static resin composition |
| WO2003040228A1 (en) * | 2001-11-05 | 2003-05-15 | 3M Innovative Properties Company | Antistatic compositions |
-
2004
- 2004-12-17 CN CNB2004800392093A patent/CN100412120C/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4450249A (en) * | 1979-08-01 | 1984-05-22 | Bayer Aktiengesellschaft | Internal antistatic agents for polycarbonates and for polycarbonate films |
| US5187214A (en) * | 1988-11-08 | 1993-02-16 | Ppg Industries, Inc. | Quaternary ammonium antistatic polymer compositions |
| EP0897950A2 (en) * | 1997-07-23 | 1999-02-24 | General Electric Company | Anti-static resin composition |
| WO2003040228A1 (en) * | 2001-11-05 | 2003-05-15 | 3M Innovative Properties Company | Antistatic compositions |
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